Oximercuration-Demercuration
Submitted by Germán Fernández on Sun, 07/15/2012 - 02:04
Treatment of an alkene with mercury acetate in presence of water produce the corresponding alcohol. This reaction is regioselective Markovnikov and stereoespecific anti.
Mechanism:
Step 1. Mercuric acetate dissociation
Step 2. Mercury cation adds to alkene with form a mercurinium ion
Step 3. Water attacks the more substituted carbon to give an alkylmercuric acetate.
Step 4. Replacement of mercury by hidrogen (demercuration)
The product obtained by oxymercuration-demercuration is the same as hydration (H2SO4 /H2O). However, oxymercuration-demercuration is not susceptible to the rearrangements.